WO 2008/112408 A1 and US 2008/0227812 A1 disclose angiogenesis inhibitors with quinoline structure, useful for the treatment of neoplasias.
One of the disclosed products is 6-(7-((1-aminocyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide of formula (I), described in example 3 of the above mentioned patent applications.

According to said documents, compound (I) is prepared by removing the benzyloxycarbonyl protective group from the compound benzyl 1-((6-methoxy-4-(5-(methylcarbamoyl)-naphthalen-2-yloxy)quinolin-7-yloxy)methyl)cyclopropyl carbamate (II):

in acid medium or by hydrogenolysis, to give compound (I).
Compound (II) is obtained in a number of steps with different processes in which the benzyloxycarbonyl protected 1-amino-1-cyclopropylmethyl moiety is introduced by subjecting the acyl azide obtained from 1-((6-methoxy-4-(5-(methylcarbamoyl)naphthalen-2-yloxy)quinolin-7-yloxy)methyl)cyclopropanecarboxylic acid of formula (III):

to Curtius rearrangement, in the presence of benzyl alcohol,
or by alkylation of 6-(7-hydroxy-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide of formula (IV):

with 1-benzyloxycarbonylamino-1-methylsolfonyloxymethyl-cyclopropane of formula (V):

The above mentioned applications do not provide yields concerning both the preparation of compound (II) by the two above mentioned reactions, and the conversion of compound (II) to (I).
Compound (III) is prepared by a process in which the 1-carboxy-1-cyclopropylmethyl moiety is introduced in 4-hydroxy-3-methoxyacetophenone as in the form of the ethyl ester, followed by formation of the 4-hydroxyquinoline ring and, finally, by the introduction of the 1-naphthylcarboxyamido fragment.
It is well known that the reactions requiring the use of azides, such as the formation of acyl azides, or Curtius rearrangement of the latter, are potentially hazardous as they involve risk of explosions, therefore they are not suitable for use in preparations on large scale.
The synthetic methods reported in WO 2008/112408 and US 2008/0227812 include, inter alia, a general synthetic scheme in which the cycloalkyl-alkyl portion of the products is introduced by reaction between a cycloalkyl-alkyl mesylate and an hydroxy or amino acetophenone, followed by nitration to give a nitroacetofenone, reduction of the nitro group to amino group, formation of the 4-hydroxyquinoline ring and further work up of the latter to the final products. The above mentioned applications do not provide examples of the use of this process for compound (I) or the other described products.